Bars with outdoor areas, patios, rooftops, retractable roofs or indoor spaces where 50 percent or more of a wall can be removed were allowed to reopen.
Tables must be spaced six feet apart and can accommodate only six people or less, and seating is limited to two hours. Alcohol sales must also end at 11 p.m. each night. Patrons are encourage to wear face masks and practice hand hygiene as well.
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"This is all I wanted, was just to sit with my buddies out at a bar or brewery and have a beer," said Andy Duerkop.
Adam Cieslak, of Maplewood Brewery and Distillery in Avondale, said reservations for their outdoor seating are already booked up into next week.
"As soon as we got the word that we could do it, we wanted to do turn it on and start getting people out here," Cieslak said. "It's awesome to see people you know, some sort of normal course of life going on."
While some bars reopened first come, first served, others say they are accepting customers by reservation only to better manage safety and health guidelines in place.
Babe's bar in Portage Park opened just in time for Diana Perez to celebrate her birthday with a beer on the patio. This is her favorite bar, and it's been a long three months waiting for it to reopen.
"All my friends are here. It's my 'Cheers' bar, if you will," said Perez.
Babe's does not serve food, so they've had zero business since mid-March. Owner Sam Belpedio said, "We've been waiting patiently for the mayor to establish the guidelines. We excited to be open after 90 days."
Neighborhood bars are a Chicago institution. Some are important gathering places that are woven into the fabric of their blocks. Sean Parnell has documented many of them in his book, "Historic Bars of Chicago."
"There's no better place to kick back and blow off some steam," said Parnell.
At Gannon's in the North Center neighborhood, the owner spent the day getting ready to open Wednesday evening. Like many small business owners, they feel like it's a victory to have survived the loss of business during the stay-at-home order. The outdoor patio seating is about a third of what they have inside, but at this point they are just glad to be back in business.
"That's why I own this business," said Sheila Murphy. "For the social aspects and to be part of our community."
Lakefront businesses hope to be next to open
In addition to bars and breweries reopening, on June 22 the Lakefront Trail will open east of Lake Shore Drive for exercise and transit only, to keep the flow of traffic going. Parks and beaches east of Lake Shore Drive will remain closed.
Chicagoans must abide by a "keep it moving" strategy where only walking, running, biking, and rollerblading will be allowed. The Chicago Park District will also install signs along the trail to encourage proper use, and Social Distancing Ambassadors will be stationed along the trail to make sure everyone is abiding by the guidelines.
Some businesses that depend on summertime income along the lakefront hope they will be next in line to open.
"We have basically between Memorial Day and Labor Day, so we have about 14-15 weeks depending on the calendar," said Robby Glick, of Reggie's on the Beach. "So it's like a third of our summer season is gone."
Reggie's on the Beach only opened at Hayes Beach House last Labor Day. Hopes for a bountiful 2020 summer season faded with restrictions due the pandemic.
"We invested a lot by doing this and we've got to try and make some of that money back and the clock is ticking," Glick said.
Chicago's lakefront beaches and beach houses do not have a date for reopening. So even with temperatures in the low 80s and a gentle breeze off Lake Michigan, there will be no outdoor dining at this lakefront restaurant. At least, not yet.
"People are allowed to have outdoor dining," Glick said. "If this isn't outdoor dining, I don't know what is."
News that the city's Lakefront Trail is reopening is hopeful news for Glick and his staff as they prepare for an eventual re-opening when the city deems it safe.
"We want everybody to be safe and healthy but we've got to get our livelihood back and we have a lot of kids that work here that are depending on us," Glick added.
Chicago's swimming pools and playgrounds will also remain closed while public health officials advise the park district on options to open them safely.
Outdoor fitness equipment, basketball courts, tennis courts and athletic fields also remain closed until further notice.
Due to the significant lakefront storm damage and high lake levels, three sections of the lakefront trail will merge to accommodate users.